#------------------------------------------------------------------------------
#$Date: 2021-03-31 00:34:56 +0300 (Wed, 31 Mar 2021) $
#$Revision: 263454 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/85/4518591.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4518591
loop_
_publ_author_name
'Cotman, Andrej Emanuel'
'Guérin, Thomas'
'Kovačević, Ivana'
'Benedetto Tiz, Davide'
'Durcik, Martina'
'Fulgheri, Federica'
'Možina, Štefan'
'Secci, Daniela'
'Sterle, Maša'
'Ilaš, Janez'
'Zega, Anamarija'
'Zidar, Nace'
'Mašič, Lucija Peterlin'
'Tomašič, Tihomir'
'Leroux, Frédéric R.'
'Hanquet, Gilles'
'Kikelj, Danijel'
_publ_section_title
;
 Practical Synthesis and Application of Halogen-Doped Pyrrole Building
 Blocks
;
_journal_name_full               'ACS Omega'
_journal_paper_doi               10.1021/acsomega.1c00331
_journal_year                    2021
_chemical_formula_moiety         'C10 H13 N O4'
_chemical_formula_sum            'C10 H13 N O4'
_chemical_formula_weight         211.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.577(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3507(5)
_cell_length_b                   13.6579(6)
_cell_length_c                   12.1808(5)
_cell_measurement_reflns_used    9819
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      2.24
_cell_volume                     2054.61(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω shuterless scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49545
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.054
_diffrn_reflns_theta_min         2.223
_diffrn_source                   'Mo-ImuS 3.0 microfocus tube'
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         6002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0509
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0594P)²+1.2668P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1414
_refine_ls_wR_factor_ref         0.1441
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5474
_reflns_number_total             6002
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao1c00331_si_003.cif
_cod_data_source_block           flik190208
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4518591
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.959
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.64143(10) 0.62176(9) 0.40978(10) 0.0165(2) Uani 1 1 d . . . . .
C2 C 0.74923(10) 0.62811(9) 0.37876(10) 0.0170(2) Uani 1 1 d . . . . .
C3 C 0.81535(10) 0.63475(9) 0.47303(10) 0.0174(2) Uani 1 1 d . . . . .
H3 H 0.8920 0.6407 0.4758 0.021 Uiso 1 1 calc R U . . .
C4 C 0.74523(9) 0.63088(9) 0.56138(10) 0.0154(2) Uani 1 1 d . . . . .
C5 C 0.53968(10) 0.61704(10) 0.34308(11) 0.0220(3) Uani 1 1 d . . . . .
H5A H 0.4788 0.6013 0.3909 0.033 Uiso 1 1 calc R U . . .
H5B H 0.5466 0.5663 0.2867 0.033 Uiso 1 1 calc R U . . .
H5C H 0.5268 0.6805 0.3078 0.033 Uiso 1 1 calc R U . . .
C6 C 0.87538(10) 0.60323(10) 0.23444(10) 0.0184(2) Uani 1 1 d . . . . .
C7 C 0.88282(11) 0.60717(11) 0.11205(11) 0.0240(3) Uani 1 1 d . . . . .
H7A H 0.9588 0.6016 0.0905 0.036 Uiso 1 1 calc R U . . .
H7B H 0.8533 0.6695 0.0855 0.036 Uiso 1 1 calc R U . . .
H7C H 0.8412 0.5530 0.0800 0.036 Uiso 1 1 calc R U . . .
C8 C 0.76630(9) 0.63080(9) 0.67867(10) 0.0160(2) Uani 1 1 d . . . . .
C9 C 0.90021(10) 0.63688(10) 0.81885(10) 0.0195(2) Uani 1 1 d . . . . .
H9A H 0.8873 0.5700 0.8471 0.023 Uiso 1 1 calc R U . . .
H9B H 0.8561 0.6835 0.8617 0.023 Uiso 1 1 calc R U . . .
C10 C 1.01824(10) 0.66253(11) 0.82844(11) 0.0229(3) Uani 1 1 d . . . . .
H10A H 1.0607 0.6168 0.7843 0.034 Uiso 1 1 calc R U . . .
H10B H 1.0414 0.6581 0.9055 0.034 Uiso 1 1 calc R U . . .
H10C H 1.0296 0.7294 0.8018 0.034 Uiso 1 1 calc R U . . .
C11 C 0.48900(10) 0.62914(9) 0.95576(10) 0.0156(2) Uani 1 1 d . . . . .
C12 C 0.38059(10) 0.63263(9) 0.98535(10) 0.0156(2) Uani 1 1 d . . . . .
C13 C 0.31515(10) 0.63329(9) 0.88997(10) 0.0164(2) Uani 1 1 d . . . . .
H13 H 0.2383 0.6359 0.8861 0.020 Uiso 1 1 calc R U . . .
C14 C 0.38652(9) 0.62932(9) 0.80278(10) 0.0152(2) Uani 1 1 d . . . . .
C15 C 0.58921(10) 0.62860(10) 1.02443(11) 0.0219(3) Uani 1 1 d . . . . .
H15A H 0.5940 0.5668 1.0650 0.033 Uiso 1 1 calc R U . . .
H15B H 0.5872 0.6833 1.0764 0.033 Uiso 1 1 calc R U . . .
H15C H 0.6525 0.6353 0.9771 0.033 Uiso 1 1 calc R U . . .
C16 C 0.25159(10) 0.61438(9) 1.12821(10) 0.0181(2) Uani 1 1 d . . . . .
C17 C 0.24206(12) 0.62118(10) 1.25023(11) 0.0230(3) Uani 1 1 d . . . . .
H17A H 0.1698 0.5994 1.2722 0.035 Uiso 1 1 calc R U . . .
H17B H 0.2531 0.6892 1.2734 0.035 Uiso 1 1 calc R U . . .
H17C H 0.2970 0.5794 1.2851 0.035 Uiso 1 1 calc R U . . .
C18 C 0.36605(9) 0.62837(9) 0.68518(10) 0.0152(2) Uani 1 1 d . . . . .
C19 C 0.23342(10) 0.62743(9) 0.54410(10) 0.0172(2) Uani 1 1 d . . . . .
H19A H 0.2602 0.5654 0.5122 0.021 Uiso 1 1 calc R U . . .
H19B H 0.2670 0.6828 0.5045 0.021 Uiso 1 1 calc R U . . .
C20 C 0.11183(11) 0.63277(11) 0.53454(11) 0.0240(3) Uani 1 1 d . . . . .
H20A H 0.0796 0.5781 0.5749 0.036 Uiso 1 1 calc R U . . .
H20B H 0.0902 0.6288 0.4570 0.036 Uiso 1 1 calc R U . . .
H20C H 0.0865 0.6948 0.5655 0.036 Uiso 1 1 calc R U . . .
N1 N 0.64131(8) 0.62244(8) 0.52144(9) 0.0161(2) Uani 1 1 d . . . . .
N2 N 0.49042(8) 0.62651(8) 0.84410(8) 0.0158(2) Uani 1 1 d . . . . .
O1 O 0.77501(8) 0.63106(7) 0.26775(7) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.94661(8) 0.57888(9) 0.29609(8) 0.0295(2) Uani 1 1 d . . . . .
O3 O 0.69681(7) 0.61991(8) 0.74830(8) 0.0228(2) Uani 1 1 d . . . . .
O4 O 0.87142(7) 0.64253(7) 0.70260(7) 0.01825(19) Uani 1 1 d . . . . .
O5 O 0.35354(7) 0.63673(7) 1.09599(7) 0.01983(19) Uani 1 1 d . . . . .
O6 O 0.17963(8) 0.59284(10) 1.06577(8) 0.0323(3) Uani 1 1 d . . . . .
O7 O 0.43657(7) 0.62432(7) 0.61568(8) 0.0213(2) Uani 1 1 d . . . . .
O8 O 0.26030(7) 0.63224(7) 0.66074(7) 0.01744(18) Uani 1 1 d . . . . .
H1N H 0.5792(18) 0.6252(14) 0.5668(17) 0.033(5) Uiso 1 1 d . . . . .
H2N H 0.5545(18) 0.6261(14) 0.7978(17) 0.035(5) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 106.39(10) . . ?
N1 C1 C5 122.40(11) . . ?
C2 C1 C5 131.21(11) . . ?
C1 C2 O1 119.64(11) . . ?
C1 C2 C3 109.40(11) . . ?
O1 C2 C3 130.90(11) . . ?
C4 C3 C2 105.60(11) . . ?
C4 C3 H3 127.2 . . ?
C2 C3 H3 127.2 . . ?
N1 C4 C3 108.46(10) . . ?
N1 C4 C8 120.48(11) . . ?
C3 C4 C8 131.02(11) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 O1 123.74(11) . . ?
O2 C6 C7 125.65(12) . . ?
O1 C6 C7 110.61(11) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 O4 123.40(11) . . ?
O3 C8 C4 124.32(11) . . ?
O4 C8 C4 112.27(10) . . ?
O4 C9 C10 106.85(10) . . ?
O4 C9 H9A 110.4 . . ?
C10 C9 H9A 110.4 . . ?
O4 C9 H9B 110.4 . . ?
C10 C9 H9B 110.4 . . ?
H9A C9 H9B 108.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 106.38(10) . . ?
N2 C11 C15 122.89(11) . . ?
C12 C11 C15 130.73(11) . . ?
C11 C12 O5 119.54(10) . . ?
C11 C12 C13 109.41(10) . . ?
O5 C12 C13 131.03(11) . . ?
C14 C13 C12 105.50(10) . . ?
C14 C13 H13 127.3 . . ?
C12 C13 H13 127.3 . . ?
N2 C14 C13 108.59(11) . . ?
N2 C14 C18 120.91(11) . . ?
C13 C14 C18 130.50(11) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O6 C16 O5 123.70(12) . . ?
O6 C16 C17 125.44(12) . . ?
O5 C16 C17 110.85(11) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O7 C18 O8 123.29(11) . . ?
O7 C18 C14 124.44(11) . . ?
O8 C18 C14 112.28(10) . . ?
O8 C19 C20 106.87(10) . . ?
O8 C19 H19A 110.3 . . ?
C20 C19 H19A 110.3 . . ?
O8 C19 H19B 110.3 . . ?
C20 C19 H19B 110.3 . . ?
H19A C19 H19B 108.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C4 110.15(10) . . ?
C1 N1 H1N 126.2(13) . . ?
C4 N1 H1N 123.2(13) . . ?
C11 N2 C14 110.11(10) . . ?
C11 N2 H2N 126.6(13) . . ?
C14 N2 H2N 123.2(12) . . ?
C6 O1 C2 119.91(10) . . ?
C8 O4 C9 115.59(9) . . ?
C16 O5 C12 120.19(10) . . ?
C18 O8 C19 115.31(9) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3601(15) . ?
C1 C2 1.3903(16) . ?
C1 C5 1.4910(17) . ?
C2 O1 1.3928(14) . ?
C2 C3 1.4053(16) . ?
C3 C4 1.3892(16) . ?
C3 H3 0.9500 . ?
C4 N1 1.3729(15) . ?
C4 C8 1.4496(16) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 O2 1.1979(16) . ?
C6 O1 1.3624(15) . ?
C6 C7 1.4956(17) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O3 1.2217(15) . ?
C8 O4 1.3373(14) . ?
C9 O4 1.4586(14) . ?
C9 C10 1.5028(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N2 1.3609(15) . ?
C11 C12 1.3909(16) . ?
C11 C15 1.4868(17) . ?
C12 O5 1.3929(14) . ?
C12 C13 1.4087(16) . ?
C13 C14 1.3881(16) . ?
C13 H13 0.9500 . ?
C14 N2 1.3742(15) . ?
C14 C18 1.4522(16) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 O6 1.2004(16) . ?
C16 O5 1.3574(15) . ?
C16 C17 1.4950(17) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 O7 1.2220(15) . ?
C18 O8 1.3377(14) . ?
C19 O8 1.4573(14) . ?
C19 C20 1.5068(17) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 H1N 0.95(2) . ?
N2 H2N 0.98(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O7 0.95(2) 1.87(2) 2.7877(14) 162.8(19) .
N2 H2N O3 0.98(2) 1.87(2) 2.8155(14) 163.4(19) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O1 -178.67(11) . . . . ?
C5 C1 C2 O1 0.0(2) . . . . ?
N1 C1 C2 C3 -1.21(14) . . . . ?
C5 C1 C2 C3 177.50(13) . . . . ?
C1 C2 C3 C4 0.82(14) . . . . ?
O1 C2 C3 C4 177.90(12) . . . . ?
C2 C3 C4 N1 -0.11(14) . . . . ?
C2 C3 C4 C8 177.39(12) . . . . ?
N1 C4 C8 O3 2.83(19) . . . . ?
C3 C4 C8 O3 -174.42(13) . . . . ?
N1 C4 C8 O4 -178.15(10) . . . . ?
C3 C4 C8 O4 4.60(19) . . . . ?
N2 C11 C12 O5 -179.46(10) . . . . ?
C15 C11 C12 O5 0.2(2) . . . . ?
N2 C11 C12 C13 -0.69(14) . . . . ?
C15 C11 C12 C13 178.99(12) . . . . ?
C11 C12 C13 C14 0.47(14) . . . . ?
O5 C12 C13 C14 179.05(12) . . . . ?
C12 C13 C14 N2 -0.07(13) . . . . ?
C12 C13 C14 C18 -179.76(12) . . . . ?
N2 C14 C18 O7 0.62(19) . . . . ?
C13 C14 C18 O7 -179.71(13) . . . . ?
N2 C14 C18 O8 -179.51(10) . . . . ?
C13 C14 C18 O8 0.15(18) . . . . ?
C2 C1 N1 C4 1.14(14) . . . . ?
C5 C1 N1 C4 -177.70(11) . . . . ?
C3 C4 N1 C1 -0.65(14) . . . . ?
C8 C4 N1 C1 -178.46(11) . . . . ?
C12 C11 N2 C14 0.65(13) . . . . ?
C15 C11 N2 C14 -179.06(11) . . . . ?
C13 C14 N2 C11 -0.37(14) . . . . ?
C18 C14 N2 C11 179.36(11) . . . . ?
O2 C6 O1 C2 -2.8(2) . . . . ?
C7 C6 O1 C2 176.94(11) . . . . ?
C1 C2 O1 C6 -157.03(12) . . . . ?
C3 C2 O1 C6 26.1(2) . . . . ?
O3 C8 O4 C9 2.86(18) . . . . ?
C4 C8 O4 C9 -176.16(10) . . . . ?
C10 C9 O4 C8 -174.04(11) . . . . ?
O6 C16 O5 C12 -2.0(2) . . . . ?
C17 C16 O5 C12 178.49(11) . . . . ?
C11 C12 O5 C16 -162.56(11) . . . . ?
C13 C12 O5 C16 18.98(19) . . . . ?
O7 C18 O8 C19 2.32(17) . . . . ?
C14 C18 O8 C19 -177.55(10) . . . . ?
C20 C19 O8 C18 179.95(10) . . . . ?
